Cesium carbonate → HCID 67413047, Verbindung

HRID 515224Notizen

Reaktionsgleichung

[F:1][C:2]1([F:27])[CH2:4][CH:3]1[CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13](B3OC(C)(C)C(C)(C)O3)=[CH:14][C:9]=2[N:8]([CH3:24])[S:7]1(=[O:26])=[O:25].Br[C:29]1[N:34]=[C:33]([CH2:35][OH:36])[CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.CCOC(C)=O.[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[F:27][C:2]1([F:1])[CH2:4][CH:3]1[CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:29]3[N:34]=[C:33]([CH2:35][OH:36])[CH:32]=[CH:31][CH:30]=3)=[CH:14][C:9]=2[N:8]([CH3:24])[S:7]1(=[O:25])=[O:26]

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide (12-1) (131 mg, 0.33 mmol, 1.0 eq), (6-bromopyridin-2-yl)methanol (61 mg, 0.33 mmol, 1.0 eq), cesium carbonate (317 mg, 0.97 mmol, 3.0 eq) and bis(tri-t-butylphosphine) palladium(0) (16.6 mg, 0.03 mmol, 0.1 eq) were combined in dioxane (1.0 mL) and water (0.2 mL). The resulting mixture was heated in the microwave at 120° C. for 20 minutes. The reaction mixture was diluted with EtOAc (10 mL), washed with water (2 mL) and brine (2 mL), dried over MgSO4, filtered and concentrated. The crude residue was purified by flash chromatography (12 g SiO2, 0-80% EtOAc in hexanes) to afford (6-{1-[(2,2-difluorocyclopropyl)methyl]-3-methyl-2,2-dioxido-1,3-dihydro-2,1,3-benzothiadiazol-5-yl}pyridin-2-yl)methanol (25-1). LRMS m/z (M+H) 382.2 found, 382.1 required.

Aufarbeitung

washwashed with water (2 mL) and brine (2 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe crude residue was purified by flash chromatography (12 g SiO2, 0-80% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-561e41129dc546d481f8a1769dff119e
Quelldatensatz: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09108937B2

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